


Don't Care if He's Guilty

by piratexchicx13



Category: Supernatural
Genre: Angst, Character Death, F/M, Fluff, Grief/Mourning, Murder, Past Character Death, Pen Pals, Prison, Protective Dean Winchester, Revenge, Sad Ending, Whump
Language: English
Status: Completed
Published: 2020-12-29
Updated: 2020-12-29
Packaged: 2021-03-11 00:08:17
Rating: Not Rated
Warnings: Major Character Death
Chapters: 1
Words: 6,702
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28395897
Author URL: https://archiveofourown.org/users/piratexchicx13/pseuds/piratexchicx13
Summary: A prison pen pal program matches Shelby with Dean Winchester, a man who’s been on death row for 5 years. He’s unlike anything she expected, and Shelby finds herself falling for the inmate.
Relationships: Dean Winchester/Original Female Character(s)
Kudos: 2





	Don't Care if He's Guilty

**Author's Note:**

> This fic was inspired by the song Don't Care if He's Guilty by The Civil Wars. It's sad and angsty and I had to write this fic.   
> I'm so sorry.

Shelby sat in the waiting room, wringing her hands nervously as she tried to block out the noise around her. Visiting hours were about to begin at El Dorado Correctional Facility, and she like many others were waiting to be let inside. Everyone else around her seemed perfectly at ease, talking on their phones or amongst themselves but Shelby imagined they’d probably been to visit before, and it was to visit someone they already knew to boot. 

This was her first visit to her pen pal Dean Winchester, and to say her nerves were rattled was an understatement. She and Dean had talked plenty in letters, and he seemed...normal. Or at least as normal as a person in prison could be. She’d yet to ask why he was in prison, let alone on death row. According to her research, it was a prison faux pas to ask why someone was serving time.

A guard announced the start of visiting hours, and the people in the waiting room formed a line to pass through the metal detector and have their belongings inspected. Another guard stood beyond the metal detector, corralling the visitors as they waited to be herded to the visiting room. Shelby made to step into the visiting room, but the guard stopped her. 

“You’re here to visit Winchester, right?” 

“Yes.” 

“This way, please.” the guard gestured down an adjacent hall, leading her into another room. A glass partition divided the room, sectioned off into stalls with concrete dividers and phones on each side of the glass. The guard directed her toward the stalls, waiting for her to take a seat before speaking into the radio on his shoulder. 

A few minutes later, the barred door on the other side of the glass opened and a guard entered with another man behind him. The guard stepped to the side, her pen pal came into view, and suddenly Shelby’s nerves were for an entirely different reason. 

Dean Winchester was gorgeous, all broad shoulders and strong thighs. 

Dean held up his hands for the guard to remove his handcuffs, rubbing his wrists as he made his way to the stall and unknowingly flexing his biceps for Shelby. Their eyes met as he reached for the phone and he gave her an easygoing smile. Good grief, his lips were sinful. His eyes were a rich, luscious green, and having them turned on her made her heart beat faster. 

Dean gestured for her to pick up her phone, and her cheeks burned red as she caught up with her surroundings and picked up the receiver. 

“Hi.” she said lamely. 

“Hey.” Oh lord, his voice was deep and smooth. 

“It’s nice to finally put a face to your letters. You’re not what I was expecting.” 

“Likewise,” Dean replied. “It’s been a long time since I’ve had a visitor.” 

“Really?” 

“Yeah, for a while my friend Bobby would come to visit but...he died a few years back.” 

“I’m sorry to hear that.” 

“I would have gone to the funeral, but you know…” Dean clicked his tongue, offering a wan smile. 

“Right,” Shelby nodded understandably. “I did some research; isn’t furlough a possibility?” 

“Not for guys like me,” Dean replied. “Especially not for guys like me.” 

“That doesn’t seem right.” Dean shrugged.

“So tell me about this research,” he said. “Didya look up what I did?” he asked, fixing her with a penetrating gaze. 

“No,” Shelby replied honestly. “No, I didn’t.”

“Why not?” Dean asked, eyebrows nearly to his hairline. “You wouldn’t want to know if, say, I murdered someone?” he pressed. 

“Dean...I didn’t sign up for this program to judge you. If you want to tell me why you’re here, I’m willing to listen, but I’m not going to pester you for details.”

“Why?” 

“What do you mean ‘why’? Isn’t it rude to ask people why they’re in prison?” Dean laughed, a full rich sound that made her cheeks turn hot. 

“So let me get this straight: you’re pen pals with a convicted felon, and you’re worried about being rude?” 

“Wh-yes! Manners are still important.” Dean laughed again, hanging his head as he chuckled. 

“You’re somethin’ else, Shelby,” he said. “Look, I’ve been on death row for five years, and your letters are one of the few things I enjoy. But I’ve never been a dishonest man, so if you want to know why I’m in here, I’ll tell you. I’d rather tell you now and have you never talk to me again than keep this goin’.” 

“Alright,” Shelby swallowed nervously. “I’m all ears.” Dean drummed his fingers on the table between them, suddenly seeming on edge.

“In my letters, I mentioned my little brother-”

“Sam,” Shelby replied. “Yes, I remember. I loved reading your stories about him.” 

“Sam is dead.” Dean said brusquely. 

“Oh my god,” Shelby gasped. “Dean-”

“Relax, Shelby, I didn’t kill him. I killed the son of a bitch who murdered him.” 

“Oh fuck.” 

“I won’t blame you if you wanna run-”

“No, no, I’m not going anywhere. Just- fuck, Dean, I don’t...I don’t know what to say. I’m so sorry.” 

“I’m not,” Dean shook his head. “Would I prefer things different? Sure. I’d rather have my brother back, and be anywhere but here. But I did the crime, so I’m doin’ the time, or however that saying goes.” he gave a soft laugh at his own joke. 

“Can I ask…”

“If I regret it? No fuckin’ way,” Dean grinned. “Ya know, they asked me the same thing at my sentencing hearing, and my answer ain’t changed. Hell, I’m not even mad they gave me the death penalty; ain’t like I got anything to live for.” 

“Dean…” 

“I mean it,” Dean said resolutely. “Sam...Sam was all I had. Our mom died when I was four, and our dad fuckin’ lost his mind; draggin’ us from one end of the country to another. We grew up dirt poor, bouncin’ from place to place. There were days I didn’t eat so Sam could. Lotta days, to tell you the truth,” Dean chuckled. “I practically raised that kid. He always got straight As in school, no matter where we were. Got himself a full ride to Stanford.” 

“That’s very impressive.” 

“Oh, man, he was the smartest person you’d ever meet. Like a walking encyclopedia. I couldn’t have been more proud.” 

“I can see why.” 

“We were thicker than thieves, me and Sam. We used to have the craziest adventures,” Dean smiled, dazzling her with his dimples. In that moment he looked younger, unburdened by his grief and life. “Even when...even when I had nothing, I had Sam,” His green eyes met hers and she could see the depth of his pain. “He was supposed to be somebody. Not a fuck up like me.”

“Dean…” Shelby reached forward, forgetting for a moment about the partition between them and hitting her knuckles on the glass.

“Look if you’re gonna say that life ain’t that bad, just leave,” Dean recoiled at her gesture of pity. “I might have time to waste in here but I’m not interested in being coddled. I killed a man and I’m on death row for it.”

“I didn’t mean to upset you; I just...I’m sorry you see yourself that way.” Shelby replied gently. Dean snorted derisively. 

“How else would I see myself?” he asked pointedly. “Sure I had a good reason, but as Jake Peralta said-”

“‘Cool motive; still murder.’” they said in unison. 

“You watch that show too?” Shelby asked eagerly. Dean shrugged.

“It was on in the rec room a few nights ago. I do like it, but I haven’t seen all of it.” 

“I would highly recommend it, if you’re able.”

“I’ll see what I can do,” Dean joked. “Where were we?” 

“You were telling me about what happened to Sam. Only if you want, of course.” 

“Someone may as well hear it. There’s not much to tell, really; we were walking out to my car one night and some lowlife piece of shit stabbed him in the back. Severed his spinal cord,” Dean looked down at the table between them, his watery eyes contradicting his matter-of-fact tone. “I mean at least I was there, right? Better than him dyin’ alone.” 

“I’m sure he was glad you were there.” Shelby said softly. Dean shrugged weakly.

“Maybe, I don’t know. He went real quick. Silver lining I guess; that he didn’t suffer. The guy who stabbed him did though.” Dean said darkly. 

“Sounds like it was well deserved.” 

“Yeah, well,” Dean cleared his throat, ducking his head as he wiped a lone tear from his cheek with the back of his hand. “Now you know why I’m on death row.” 

“Ten minute warning!” the guard behind Dean yelled. 

“Oh wow,” Shelby laughed. “Time flies when you’re having fun, I guess.” 

“Always does.” 

“I don’t want to end on a sad note.” 

“Tell me about you, then. I feel like I’ve talked more than my fair share.” 

They spent the last ten minutes of visitation talking about Shelby’s family, her annoying coworkers and her nana’s secret barbecue sauce recipe. 

“I wish I could make it for you.” Shelby said. “I love cooking for people.” 

“Like on a date?” Dean asked. “Sorry, that was presumptuous.” he added sheepishly.

“No, it’s okay,” Shelby smiled. “Barbecue is a perfect date food.” 

“A rain check, then,” Dean teased. “I do love barbecue though,” he sighed wistfully. “The food here sucks.” 

“What do you miss the most? I’ll make it for you.” 

“The most?” Dean sat back in his chair, rubbing his fingers over his stubble. “Oh man, I don’t know. I was always a beer and burgers kinda guy, but I love me some pie.” 

“Pie it is,” Shelby grinned. “It was really nice to meet you, Dean.” 

“It was nice to meet you too, Shelby.”

“Would it be okay if I came back next week?” 

“Next week?” Dean tapped his fingers to his chin. “That’s the 11th, right? Darn, I’ll be in Barbados that day.” he joked. 

“Guess you won’t be getting pie then.” 

“I won’t be getting pie either way, sweetheart. But I appreciate the thought. See you next week.” 

“Take care, Dean.” 

“You too.” 

Shelby settled into a new routine: she’d go to work through the week, and trade letters with Dean. Saturdays were visiting days. Every weekend she’d make the trek to see him in person and they’d spend an hour sharing stories and making each other laugh. It was the highlight of her week. Her friends didn’t understand why she was spending so much time with ‘that weird guy in prison’, but she just ignored their naysaying.

The seasons changed, the weather cooling as autumn arrived and her birthday neared. She arrived for visitation one day to be greeted by Dean wearing a birthday hat. A guard handed her one as she sat down and picked up the phone. 

“Thank you Bill, but um...what is this?” she asked, picking up the hat between two fingers. 

“It’s the most I could do for your birthday,” Dean replied. “Sue me, I wanted to do something nice.” 

“Dean.” 

“Yeah, you’re right. Not much good suing me will do ya anyway; I’m already on death row.” 

“Dean, that’s not funny.” 

“Sure it is! I’m hilarious.” 

“You’re ridiculous,” Shelby laughed. “This is really sweet.” 

“You don’t have to wear it if it’ll mess up your hair or anything-”

“Nonsense,” Shelby stuck the party hat on her head with a giggle. “You know what we need? Snacks.” 

“You read my mind,” Dean chuckled. “Are you a savory or sweet person?” he asked. 

“Yes,” Shelby laughed. “One second.” she put the phone down and approached Bill, asking him something Dean couldn’t hear. Whatever it was, Bill must have agreed, because Shelby lit up and darted back to her seat. 

“What kind of snacks do you like?” she asked eagerly. “Bill said he could give you something if it came from the vending machines out here.” 

“Seriously?” Dean scoffed, quickly deciding not to look a gift horse in the mouth. “Fuck, uh…jerky. Seriously, any kind. And gummy bears.”

“You got it.” Shelby abandoned the phone again and went back to Bill with her purse. Dean was able to see her feed money into the vending machine and hit the buttons, handing packages to Bill before putting in her own order. 

She returned with a package of Cheez-Its and a Reese’s. 

“Are you kidding me?” Dean teased. “Cheez-Its? Lame.” 

“Shut up; they’re white cheddar,” Shelby scoffed. “And don’t even try to insult my candy choice.” 

“Why would I do that?” Dean asked innocently. “Chocolate and peanut butter are the superior flavor combo.” 

The door behind Dean opened and Bill entered the little visiting area with Dean’s goodies from the vending machine. 

“Would you take a picture with me?” Shelby asked suddenly, catching Dean off guard. 

“I’d rather not,” he shook his head, smiling apologetically. “Orange is hardly a flattering color.” 

“I bet you just don’t want people to see with that hat.” Shelby snickered. 

“You’re gonna show it to people?” Dean asked incredulously. 

“Not a lot of people,” Shelby replied. “I won’t if you don’t want me to, I was just planning to show you off to my friends.” 

“Oh yeah? Do they ask about me?” 

“They didn’t believe me when I told them how handsome you are,” Shelby grinned when Dean’s cheeks went pink. “They uh...they all think I’m crazy for coming to see you every weekend.” she added shyly. 

“Can’t say I blame ‘em. Pretty girl like you should be out living your life instead of in this tomb with me.” 

“I’m exactly where I’d like to be, Dean. I like spending time with you. I care about you a lot, and judging by how silly you look right now, I’d say the feeling is mutual.”

“Hey!” Dean protested, making Shelby laugh. 

Dean eventually agreed to take a selfie with her, party hat and all. 

The following week was uneventful. Shelby met her friends for drinks on Friday evening, and they grilled her non-stop about Dean. 

“I don’t understand how you waste your Saturdays in  _ prison _ ,” her best friend Michelle sneered. “You’ve been blowing us off for weeks, and we’re all concerned.” she gestured to the two women flanking her.

“Just because I don’t go shopping or to brunch every Saturday doesn’t mean I’m blowing you guys off,” Shelby replied. “And I’m not  _ wasting _ anything. I like spending time with Dean.” 

“So what you’re saying is you like hanging out with a murderer more than your friends.” 

“Whoa-” 

“Are you seriously gonna try to defend him?” her other friend Blair asked accusingly. “What kind of spell does he have you under?”

“Oh, I can guess,” Michelle said smugly. “Conjugal visits are still a thing, are they not?” Blair gasped in shock.

“Tell me you’re not fucking a literal murderer!” 

“Stop calling Dean a murderer. That’s not okay-”

“But that’s  _ literally  _ what he is-”

“Shove it up your ass, Blair,” Shelby seethed. “You two are being such assholes right now. Yes, Dean is in prison and yes, it’s for murder, but neither of you know the full story so stop blindly assuming he’s a shit person. I’m sorry if you feel like I’ve neglected you. I agreed to come out tonight because I felt bad, but if all you’re going to do is talk shit, I’m going home.” 

“I can’t believe you’re defending a murderer.” Shelby rounded on her friend, tossing her drink in the woman’s face. 

“Shut the fuck up, Michelle. You know nothing about Dean. How dare you judge him. If you took any time at all to know him, you’d know what kind of person he really is,” She fumed. “Anything you wanna add?” she asked her third friend Casey, expecting her to pile on some hateful comments of her own. 

“Nope. Great job. Let’s go,” Casey slid out of the booth and got to her feet. “Shove it up your cunts.” she flipped off Blair and Michelle before she and Shelby left the restaurant. 

“You didn’t have to do that.” Shelby said as they stepped outside. 

“Yeah, I did. They shouldn’t have said those things,” Casey replied, as if ending two years-long friendships was no big deal. “Michelle and Blair are bitches anyway.” 

“Yeah they are.” Shelby couldn’t help but laugh. Michelle had looked pretty funny drenched. 

“So this is awkward...Blair was actually my ride home,” Casey said. “Any chance I could catch a lift with you?”

“Yeah of course,” Shelby agreed easily. “You know, we didn’t actually get to eat; do you wanna grab takeout and come hang at my place?” 

“Sounds great.” 

Half an hour later found the pair at Shelby’s home, sitting on the floor eating pizza while they watched a movie. Casey ended up staying the night, passing out on Shelby’s couch during their third movie.

The following morning they were eating breakfast in Shelby’s kitchen, and Casey could visibly see the excitement in Shelby. She was due to leave to visit Dean soon, but they still had some time before she had to go. 

“So tell me about Dean,” she said suddenly. “Not the Dean everyone thinks they know. Your Dean.” 

“He’s not exactly ‘my’ Dean.” Shelby objected.

“You know what I mean. It’s obvious you care about him.” Shelby smiled, ducking her head as her cheeks warmed. 

~~~~

“You guys write letters too? That’s so cute.” Casey cooed.

“Shut up!” Shelby laughed. 

“I’m serious. It’s adorable,” Casey said. “You see each other every Saturday but you still write letters through the week. It’s like an old timey love story,” she swooned. “I don’t wanna be nosy, but I’m dying to know what they say.” 

“I don’t have mine, obviously, but I have the ones he’s sent me,” Shelby hesitated. “So I probably don’t need to say this but they really mean a lot to me. Promise you won’t laugh or anything?” 

“Promise.” Casey drew an X over her heart. 

~~~~

El Dorado Correctional Facility- that same morning

Dean was reading in his cell when a guard banged on the bars.

“Winchester. Let’s go.” the guard said. 

“Sure,” Dean replied, as if he had a choice. “What’s up?” 

“Warden wants to talk to you.” the guard replied as Dean put his hands through the little window to get handcuffed. He was glad it was this particular guard escorting him. 

The guard escorted him through the prison and up to the administrative offices, opening the door to the warden’s office and stepping inside, closing it behind them both. 

“Mr. Winchester,” the warden looked up from his stack of paperwork to greet him. “Good morning.” 

“Good morning, sir.”

“Please sit,” the warden said warmly. Dean obliged, sitting in the chair in front of the warden’s desk. “I’m sure you’re wondering why I had you brought here.” 

“I can guess, sir.” 

“Since your execution date is approaching, I wanted to go over your final arrangements with you and make sure everything is in order.” 

“Oh,” Dean said flatly. “Right. Well uh...what would you like to know?” 

“Have you given any thoughts to bequeathments?” the warden asked. 

“Yeah, uh...I want to leave everything to my...penpal, Shelby.” 

“The young lady who’s come to visit you every weekend for months now?” the warden asked. 

“Yes sir.” 

“‘Pen pal’ seems a little impersonal.” 

“Well in light of...things, it uh...well, there’s really no point, is there?” Dean asked. 

“There’s always a point, Winchester,” the warden said somberly. “So...everything to Miss Warren, then. Your personal items, including your car?”

“Yes sir. She needs it more than me,” Dean smiled wanly. “Her poor little Buick is a piece of trash.” he chuckled. 

“As you wish,” the warden made a note on the legal pad. “On your health forms you checked ‘cremation’, is that still your wish?” 

“Yes sir.” 

“Now about your last meal,” the warden pressed on. “Any requests?” 

“Actually...I had an idea that I wanted to run by you...if that’s okay.” Dean said hesitantly. He knew the warden sympathized with his situation, having been told so by the warden himself when he first arrived at the prison. He’d been a model inmate, never caused trouble and tried his best to stay away from those who did. 

The warden sat back in his chair, regarding Dean coolly. Dean swallowed nervously, knowing he most likely wouldn’t get what he was asking for. 

“I’m listening.” 

~~~~

When Shelby arrived at the prison, everything seemed normal. She saw the same people in the waiting room, had her bag checked by the same guard, was escorted to the visiting room by the same guard.

The first noticeable difference was Dean. She could see him practically vibrating with excitement as his handcuffs were removed and he made his way to the little booth where she sat.

“I have a surprise for you.” Dean said the instant he picked up the phone. Excitement was written all over his face; his eyes were lit up like a child’s as he smiled. 

“What is it?” 

“Go with Bill, okay? I’ll see you in a minute.” 

“Dean, what-” Dean hung up his receiver and went back to the guard who’d just taken off his handcuffs and held his hands out. Shelby watched the guard put the cuffs back on Dean and escort him from the room. Confused, Shelby flinched when Bill appeared at her side. “Bill, what is going on?” 

Bill just smiled and gestured for her to head toward the lobby. Shelby grabbed her purse from the floor and followed Bill’s directions as he led her deeper into the prison. He finally ushered her into what Shelby assumed was the guard’s break room. 

The table was laid out with a checkered tablecloth (Shelby couldn’t be sure if that was special or not) and a picnic basket. A vase stood beside the basket, holding a single daisy, Shelby’s favorite. 

There was a commotion from the doorway and Shelby looked over to see Dean, not behind glass for the first time. 

“Dean!” Tears stung Shelby’s eyes, obscuring her vision as Dean’s handcuffs were removed. “Hi.”

“Hi yourself.” Dean looked quite pleased with himself. 

“Hi,” Shelby repeated, her mind unable to come up with any other words. “Sorry, I’m just...you’re here, right in front of me.”

“Ta da…” Dean said shyly, grinning when Shelby laughed.

“Standard visit rules,” Bill said from the corner. “One hug at the beginning of the hour, one at the end.” 

“Is that okay?” Dean asked hesitantly. “I didn’t want to assume-”

“Of course it’s okay,” Shelby wrapped him in a hug, sensing he was feeling shy. After a moment’s hesitation, Dean wrapped his arms around her and held her close. Dean was warm and solid, finally,  _ finally  _ tangible in her arms. “This is nice.” she added feebly. Nice couldn’t begin to cover how happy she was. That happiness was shared by Dean, judging by how tightly he squeezed her. 

“It is,” Dean said softly, tucking her head under his chin as she clung to him. Behind them Bill cleared his throat, and Shelby immediately remembered there was another person in the room. “Here, we should sit.” Dean pulled out a chair for her, smiling when she turned her back to him to sit down. He’d seemed scared to touch her, as if he’d expected her to shy away from his touch. Shelby trusted Dean absolutely and would do what she could to show it. 

“So...what’s the occasion?” she asked when he’d sat down across from her. 

“I just thought it would be nice. It’s the closest thing to a real date I can swing,” Dean shrugged, avoiding her gaze. Shelby got the impression there was something on his mind, but knowing Dean he wouldn’t tell her. “Just...don’t get used to it, ‘kay? You have no idea how much groveling I had to do to get this set up.” he added teasingly. 

“Okay, forget I asked,” Shelby backtracked, deciding to leave it alone. “I would have brought pie if I’d known.” 

“But then it wouldn’t have been a surprise,” Dean laughed. “Besides, I’m pretty sure there’s one in the basket. But first- did you see the daisy?” 

“I did, and I love it,” Shelby swooned. “You remembered.” 

“Of course. I remember everything about you,” Dean smiled warmly. “Do you wanna wear it?” he asked. 

“I’d love to.” Shelby beamed, watching Dean as he plucked the flower from the vase and fashioned it so it could be tucked behind her ear. His hands were warm as he gently put it in place, fingers trailing along her jawline as he gazed at her appreciatively. 

“There. You look beautiful.” 

“Thank you, Dean.” 

“You’re welcome,” Dean smiled proudly. “So, are you hungry? There should be stuff to make sandwiches.” 

~~~~

The klaxon announcing the end of visiting hours sounded and Shelby’s heart sank. Dean pursed his lips thoughtfully when Bill told them it was time to say their goodbyes. 

“Bill can you give us a minute?” he asked. Bill shot Dean a knowing look but obliged, turning his back to the table to stare at the cabinets. This time Dean drew Shelby into the hug, holding her like a cherished treasure as she wound her arms around his neck. 

“Are you going to kiss me, Dean?” Shelby asked leadingly. If this could only happen in front of Bill, then so be it. 

“Maybe,” Dean offered shyly, licking his lips as he looked down at her mouth. “Guy can dream, right?”

“I think we can do better than that.” Shelby snickered, raising up on her tiptoes to close the distance between them. Dean’s lips were soft and warm, and he tasted like pie. His hands fisted in her dress as he pulled her flush against him, claiming her mouth in a heady kiss as she anchored herself by tangling her fingers in his thick hair. Shelby was grateful for Dean holding her upright; she’d surely be on the floor without his support. 

Bill cleared his throat, and Shelby felt her cheeks turn red. Dean loosened his grip on her, giving her another kiss as she relaxed. He leaned down, resting his head against herself as she hugged him around the waist. 

“I’m really glad we did this.” he said softly. 

“Me too,” Shelby said into his chest as the door to the room opened. “Best date ever.” 

“Hardly,” Dean laughed. “I’m glad you enjoyed it though.” he smiled widely. 

“Time’s up. Time to go, Winchester.” the newly arrived guard announced. Shelby saw Dean’s face harden before he nodded. He gave her a quick kiss on her forehead before pulling away from her, obediently holding his wrists out to be handcuffed. 

“Step back, please, miss.” the new guard asked. 

“I wish I could take you with me.” Shelby blurted, suddenly cold in the wake of his departure. 

“No, you don’t. I snore,” Dean joked, giving her a smile that didn’t reach his eyes. “Drive safe, sweetheart.” 

“Always. See you next week.” Shelby took a step back as asked, 

“Take care of yourself, Shelby.” Dean said, following the guard out into the hallway. As quickly as he’d arrived in front of her, Dean was out of her line of sight, and Shelby felt tears threaten. This entire situation was so unfair. 

Bill touched her elbow gently, giving her an apologetic look. 

“Sorry, Bill.” she said wetly, doing her utmost to collect herself. She’d had a great time with Dean, better than usual, and she should focus on that. 

“It’s alright, ma’am. Would you like assistance getting to your car?” the guard asked kindly. 

“No, thank you. I’ll be fine.” 

Shelby cried the entire way home, and immediately called Casey to tell her everything. She told her about the surprise picnic, and the daisy, and how thoughtfully and reverently Dean treated her, and cried some more. 

“It sounds like you really love this guy.” Casey offered sympathetically. 

“I really do.” Shelby hiccupped, smiling widely despite the tears on her face. Despite all obstacles, she loved Dean Winchester. 

Shelby connected with Dean on a level she’d never connected with anyone. She felt she could tell him anything; knew him like the back of her hand and felt like, were circumstances different, she could spend a lifetime loving him and being loved in return. On Monday she sent Dean a new letter telling him how she felt, and waited on pins and needles for his reply. 

A reply didn’t arrive the following day as she’d expected. Shelby couldn’t help but be disappointed; Dean was always so quick to reply. Maybe she should have waited to tell him about her feelings for him until she saw him on Saturday. Anxiety kept her awake that night, and for the following two nights she slept poorly. 

On Friday, after four days of no response from Dean and kicking herself for sending that last letter, someone knocked on her door. Puzzled, Shelby put the mop back in its bucket and made her way to the living room. 

“Yes?” She didn’t recognize the man on her porch, but she recognized the federal corrections logo on his shirt. 

“Shelby Warren?” the man asked. At his side he held a cardboard box with a smaller box on top, and had a clipboard tucked under his arm.

“Yes, that’s me. Can I help you?” 

“I’ve been asked to deliver these items to you. They were Dean Winchester’s possessions and he bequeathed them to you.” 

“I don’t understand,” Shelby shook her head. “Is Dean okay?” 

“His sentence was carried out Wednesday morning.”

“What?!” Shelby’s stomach dropped, and tears welled in her eyes. “Dean’s dead?” 

“Yes ma’am,” the man at least had the decency to look apologetic. “I’m sorry for your loss. Um...these are his things and his...his ashes.” he offered the boxes to her, ducking his head when she reached for them. 

“But- why didn’t he say anything? He knew, right?” Shelby hugged the boxes tightly. 

“The date has been set for a while, but I couldn’t tell you why he didn’t mention it.” 

“What am I supposed to do?” Shelby asked with a sob. “I don’t know what to do.” 

“I think he wrote you a letter before...before,” the man cleared his throat awkwardly. “He also bequeathed you his car, but it won’t be here until tomorrow.”

“His car?” Shelby hiccupped, clutching the box to her chest. “The Impala?” 

“Uh…” the man checked his clipboard, lips moving as he read silently. “Yes. 1967 Chevy Impala, black. Could I have you sign here please?” he asked, holding out the clipboard and a pen for her to sign his form. Shelby shot him a withering stare.

“You’ll have to excuse me. My hands are a little full.” she let the door slam behind her as she went back inside, eyes darting around as she looked for a place to put the box down. It felt strange to think she was setting Dean on her dining room table, and another wave of tears spattered on the boxes when she sobbed. 

Shelby pulled herself together long enough to sign the man’s form and slam the door in his face again, leaving her alone with the box of Dean’s things and his ashes. She rested against the door for a moment, heart beating out of her chest as the items loomed large. 

Pushing off the door she rummaged through the box for the letter, fingers inching past a flannel to clasp a crisp envelope. 

“I need a fucking drink.” Shelby raced to the kitchen and poured herself a tumbler of whisky to calm her nerves. She leaned against the counter and sank to the floor, hands shaking as she opened the envelope. 

Shelby,

Shelby’s chin wobbled as fresh tears eroded her vision. A sob escaped her throat and she took a gulp of whisky, grateful for the burn of the alcohol to ground her. She opened the letter and tried to read a second time. 

_ Shelby,  _

_ I wish I had more time to write this letter. I have a lot of apologies to make and not much time to make them.  _

_ I’m sorry I didn’t get to taste that pie you promised me (I swear that’s not a dirty joke (okay, it kind of is haha)). I’m sorry for not answering your letter earlier this week. Even though the feeling is mutual, I needed some time to come up with a proper response. (I wish more than anything it could have been given in person.) _

_ I’m sorry I have nothing to offer you. Even if I wasn’t in prison, I wouldn’t have much to offer you. I’m a high school dropout with very little money to my name, and no ‘real world’ skills. As it is, I’ve left all of my things to you, and I know that little box is underwhelming.  _

Shelby’s eyes darted to the box of Dean’s things. She sniffled, wishing she could tell him nothing about him was underwhelming. 

_ I’m not usually one to dwell on what-ifs but I wouldn’t feel right if I made that final walk without telling you how I feel about you. If things were different-Sam dying, me being in prison for murder, all of it- I’m struggling to think how our paths would have crossed, but maybe we’d meet at a bar or something basic like that (sorry I’m boring). I would have liked to spend more time getting to know you inside and out (sorry, I know that probably sounds dirty but I don’t mean it in a disrespectful way). In the short time I’ve known you I’ve learned that you’re sweet and bake pie when you can’t sleep and for some reason, you’re interested in a dope like me. I can’t fathom what a girl like you sees in a guy like me, but if I could I’d stick around for the long haul to find out.  _

_ I’m also sorry I didn’t tell you this was coming. I feel like an asshole for not giving you any warning, but if I could argue in my defense...how does a guy say something like that?  _

_ I won’t lie and say it’s better this way, because there’s no ‘better’ here. I’m sorry for that too, by the way. I can’t imagine how awful it’ll be for you to get my box of stuff and my ashes (fuck, my ashes) and this shitty letter. I’m grateful I at least got to spend some time with you without glass in between us. As far as last meals go, that one was pretty great.  _

_ I have no right to dump this on you. I feel awful doing it, but you’re all I’ve got left. I won’t make any demands; I have no right to do that to you. But...if it’s not too much trouble, could you take my ashes to Memorial Park Cemetery? My parents and Sam are buried there and it would be nice to be with them.  _

_ As for the box, you can keep whatever you want. It’s just clothes. The necklace doesn’t really have any value beyond sentimental; it’s something Sam gave me for Christmas one year when we were kids. You can keep Baby too, if you want. I know you said your car was giving you some trouble and Baby has never let me down. She’ll take care of you since I can’t.  _

_ Shit, it’s time for me to go. Try not to think about it too much, okay? I’m gonna be okay. Thank you for everything.  _

_ Love (?) _

_ Sincerely _

_ Love,  _

_ Dean Winchester _

~~~~

“Well, here we are,” Shelby said to the empty car as the wrought iron gates for Memorial Park Cemetery loomed overhead. She looked over at the passenger seat, the seatbelt keeping the urn safe and secure. “You’re probably ready to be here, I bet. Probably sick of my house.” she chuckled to herself. 

It felt strange to be outside of the house. She’d been in isolation for over a week processing her grief. She was nowhere near the end of her process by any means, but it was time for her to honor Dean’s request and put his ashes with his family. Casey had offered to make the trip with her, but Shelby had politely declined. This was something she needed to do on her own. 

Stranger still was the fact that she was driving Dean’s car. It was a little dusty from sitting in impound for so long, but the love and care Dean had put into the car was clear. It was easy to imagine Dean driving the car, running his hands along the steering wheel lovingly. He’d said once that driving a deserted highway, just him and Baby and some Zeppelin, was his idea of heaven. Shelby hoped that wherever Dean was he’d gotten his wish. 

Pulling through the gates, Shelby felt oddly nervous. In a way this was like a ‘meeting-the-family-for-the-first-time’ event, and Shelby hoped that Dean’s family could get some closure now that he was coming to join them (if that was even possible; did people need closure after they’d died? Ghosts might, but Shelby dismissed that line of thought before it got any further. No thinking about ghosts in a cemetery. 

Shelby spotted ‘Winchester’ out of the corner of her eye and hit the brakes, her right hand shooting out to brace the urn. 

“Sorry,” she apologized for the abrupt stop, both to the car and the urn. She gazed out of the window, eyes squinting in the bright sun, peering amongst the headstones until she found the marker she was looking for. “Yep, there it is. C’mon Dean, let’s get you where you wanna go.” She shut off the car and leaned over to get the urn, unbuckling it carefully so the buckle didn’t hit it. She cradled Dean to her chest and climbed out of the car, Dean’s necklace tap-tap-tapping against the urn as Shelby stepped from the even asphalt to the uneven grass. Shelby made her way through the headstones, careful to avoid stepping on anyone as she approached the Winchester marker. 

“Um...hello, Sam. Dean told me a lot about you,” she said awkwardly to Sam Winchester’s headstone. The plot to the left bore the names Mary Winchester and John Winchester, and Shelby gave a feeble grin. “These must be your parents,” she said softly. “It’s a regular family reunion, huh? Wow, Shelby, that was a terrible thing to say. Jesus,” she looked down at her feet. “Here, I’ll put you on Sam’s headstone, huh? That way you’re in the middle, surrounded by family. Look, there’s even shade!” Shelby said cheerfully, sniffling as she knelt between the graves and set Dean’s urn on Sam’s headstone. “Brings a whole new meaning to the phrase ‘got it made in the shade’,” she joked, laughing wetly. “Wow, I’m just full of awful jokes today. Clearly humor is my coping mechanism,” she said to the urn. “I’m so sorry things went this way, Dean. You deserved so much better,” she chewed on her lip, feeling unable (and unwilling) to say goodbye and leave. “I hope wherever you are is really nice. You deserve that. But I know you; you’d be worrying about me and Baby. I promise we’ll be okay. Might take a while, but we’ll be okay. Just...I guess tell everyone hi from me, and maybe...maybe we’ll bump into each other somewhere down the road.” 

No answer came from the urn (not that she expected any), but Shelby got the feeling that somewhere Dean was urging her to get the hell out of the cemetery and go live her life. 

“Goodbye Dean.” Shelby got to her feet and made her way to the car, looking back tearfully when she got into Baby. A balmy breeze picked up, rustling the leaves and parting the clouds. A drop of sunshine reflected off the urn, and Shelby smiled, knowing it was Dean’s way of letting her know he was okay. She started the car and used the sleeve of his flannel to wipe her face as the engine roared to life.

**Author's Note:**

> Noooooo poor Dean!!!  
> Are we still friends? Do you hate me?? Was this fic too soon after that-episode-which-shall-not-be-mentioned? Let me know! I love feedback. It sustains me :)


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